Could be vapor lock, or the gas is percolating out of the carb. Where is the tank, higher or lower than the fuel pump? 8 pounds is too much for an Eddy, they work better with 3 or 4, maybe flooding when shut down hot? Could try an electric pump, switch it on when the starting problem arises, if it's starving. First you should find out if it's flooding or starving, try priming it next time, see if it starts better then. Kind of a rambling answer, but you left out a lot of info, hard to be specific.